‫ﺟﺎﻣﻌﺔ ﺳﻔﻧﻛس‬

‫ﻛﻠﯾﺔ طب اﻻﺳﻧﺎن‬

Chemistry of Carbohydrates II
Objectives
• Define chemistry and functions of some
disaccharides.
• Define and classify polysaccharides.
• Discuss structure and functions of medically
important homo- and hetero-polysaccharides.

Prof. Abd-ElRaheim Meki

Dr. Eman Magdy Radwan
Biochemistry Dept, Sphinx University
 Disaccharides
a) Maltose (malt sugar):
• It is a disaccharide that consists of 2 glucose units linked by alpha (a) 1,4-
glucosidic linkage.

•It has a free aldehyde group so it is a reducing

sugar.

•It is hydrolyzed in human intestine by maltase enzyme.

Maltase
2. Maltase (α-glucosidase): Maltose Glucose + Glucose
b) Lactose (Milk sugar)
• It is a reducing disaccharide that consists of glucose and galactose linked by beta (b)
1,4-glucosidic linkage.

• It is digestible in human intestine by lactase enzyme.

Lactase
1. Lactase (β-galactosidase): Lactose
Lactose
Glucose + Galactose
Glucose + Galactose
It is the most suitable sugar for baby feeding as a sweetener for milk :
ØIt is the least sweet sugar, so the baby can nurse a large amount of
mother’s milk without getting his appetite lost.
ØIt is non-fermentable because it has a b-glycosidic linkage, so it does
not form gases and does not cause colic to the infant.
ØIt has a laxative effect, prevents constipation and is non-irritant to
the stomach.
ØIt helps in the absorption of the calcium of milk.
c) Sucrose (Cane or Table sugar):

• It is formed of a-glucose linked to b-fructose by a-b-1,2-

linkage. It is hydrolyzed by sucrase enzyme.
• The 2 active carbons (C1 of glucose and C2 of fructose)
are in the linkage, therefore it is a non-reducing sugar.

d) Cellobiose:
• It is formed of 2 b-glucose units linked by b-1,4-
CH2OH
glucosidic linkage. CH2OH
O O
H OH
H
• It is the building unit of cellulose. H
1 O 4 H
H
OH H OH H
OH H
• It is a reducing disaccharide.
H OH H OH
• It is non-fermentable and indigestible. b-Glucose b-Glucose
Cellobiose
 Polysaccharides
Polysaccharides are sugars that contain more than 10 monosaccharide units per
molecule, they are classified into:

Polysaccharides

Homopolysaccharides Heteropolysaccharides
They yield only one type They are polysaccharides that
of monosaccharides on on hydrolysis produce several
hydrolysis types of sugars.
 Homopolysaccharides
named according to the type of Hexosa
monosaccharide
Homopolysaccharides ns
named according to the type of Hexosa
monosaccharide ns

Glucosans Fructosans Galactosans

Glucosans Fructosans Galactosans

Starch, Agar
Glycogen Inulin
Agar
&
Starch,
Cellulose Agar
Glycogen Inulin
Agar
&
Cellulose
 Homopolysaccharides
I. Glucosans:
a) Starch
• It is the stored form of carbohydrate in plants (storage polysaccharide). It doesn’t
exist in animals.

• Starch granules are formed of:

Ø The core amylose (20%): A straight chain compound formed of a large number of
a-glucose units linked by a-1,4-glucosidic bond.

ØThe shell amylopectin (80%): Branched chains formed of a large number of a-

glucose units linked by a-1,4-glucosidic linkage along the branch and by a-1,6-
glucosidic linkage at the branching point that occur periodically every 25-30
glucose units.
 CH2OH 6CH OH CH2OH CH2OH CH2OH
2
O 5 O H O O H H O H
H H H H H H
H H H H H
OH H 1 4 OH H 1 OH H OH H OH H
O O O O OH
OH 2
3
CH 2OH CH 2OH
H OH H OH H OH H OH H OH
O O
H
H
H H
H
H

1
amylose
H 1 4 OH
OH
O
O

H OH H OH n
Amylose

CH2OH CH2OH
H O H H O H amylopectin
H H
OH H OH H 1
O
OH
O
H OH H OH

CH2OH CH2OH 6 CH2 CH2OH CH2OH

H O H H O H H 5 O H H O H H O H
CH 2OH H H H H H
CH 2OH
OH H OH H OH H 1 4 OH H OH H
O
4 O O
O H O O OH
H H OH 2
H H 3
1 4 1 H OH H OH H OH H OH H OH
OH H OH
O
O
H OH H OH
Starch is digestible by human amylases (Salivary and Pancreatic) which
hydrolyze a-glucosidic linkage into dextrins that are further hydrolyzed into
maltose and isomaltose.

& Isomaltose
b) Glycogen:
• It is the stored form of carbohydrate in animal, particularly in muscles and liver.
• Its structure is similar to amylopectin a branched tree with a-1,4-glucosidic
linkage along the branch and a-1,6-glucosidic linkage at the branching point.
However, the glycogen tree is shorter and more branched (a branch point every
8-10 glucose units) than amylopectin.
• Glycogen is hydrolyzed by amylases.

CH 2OH CH 2OH
H O O
glycogen
H H H
H H
OH H OH H 1
O
OH
O
H OH H OH

CH 2OH CH 2OH 6 CH 2 CH 2OH CH 2OH

H O H H O H H 5 O H H O H H O H
H H H H H
OH H OH H OH H 1 4 OH H OH H
4 O O
O O OH
OH 2
3
H OH H OH H OH H OH H OH
c) Cellulose:
• It is a structural polysaccharide. It forms the skeleton of plant cells and does not enter
in animals cell structures.
• It is a straight chain molecule formed of a large number of b-glucose units linked by b-
1,4-glucosidic linkage.
• It is indigestible in humans because of the lack of enzymes that hydrolyze b-glycosidic
linkage. It gives cellobiose on hydrolysis with HCl.

CH2OH 6CH OH CH2OH CH2OH CH2OH

2
O 5 O O H O H O OH
H H H
H H H H H
OH H 1 O 4 OH H 1 O OH H O OH H O OH H
OH H H H
H 2 H
3
H OH H OH H OH H OH H OH
cellulose
 II. Fructosans
• Inulin: is formed of fructose only
• It is present in onions.
• It is not metabolized in human body; therefore, it is used in
evaluation of kidney function (inulin clearance test).

III. Galactosans

• Agar-Agar: is present in seaweed.

• It is used for growth of bacteria cells in culture.
 Heteropolysaccharides

Nitrogenous
Contain sugar-amines

Acidic Nitrogenous (uronic acid)

Neutral Nitrogenous Mucopolysaccharides/
Glycosaminoglycans/ Proteoglycans
Glycoproteins

Sulfur Free: Sulfated:

Hyalouronic acid Heparin
 I. Nitrogenous Heteropolysaccharides:
A. Neutral Nitrogenous Heteropolysaccharides
Glycoproteins:
• They do not contain uronic acids or sulfate groups.
• They are formed of a large protein core to which branched chains of
carbohydrate (oligosaccharides) are attached.
• Different carbohydrates present include sugar
amines, hexoses, pentoses, and deoxy sugars as Glycoproteins
fucose.
Function: Glycoproteins are found in:
1. Mucins of saliva
2. Cell membranes
3. As a part of collagen of connective tissue
 B. Acidic Nitrogenous Heteropolysaccharides:
Proteoglycans:
• They consist of very small core protein molecule to which a huge carbohydrate
tree is attached.
• The carbohydrate moiety is a linear polysaccharide made up of repeating
disaccharides. It is called mucopolysaccharides or glycosaminoglycans (GAGs).

Functions:
• GAGs are components of the connective tissue including the organic matrix of
dentin.
• GAGs are components of cell membranes. Peptidoglycans are constituents of
the cell walls of oral bacteria.
I. Sulfur free Mucopolysaccharides: Hyalouronic acid

Function:
1. It is present in connective tissue matrix, around the ovum, and in
vitreous humor of the eye to preserve their structure.
2. It is present in the synovial fluid for lubrication (Incompressable).
II. Sulfur containing Mucopolysaccharides: Heparin:

• Function:
It is an anticoagulant. It inactivates thrombin and coagulation factors IX and XI.
It is used in cases of increased coagulability as in deep venous thrombosis.
Test yourself
1. The polysaccharide used in assessing the kidney function is:
(A) Glycogen (B) Agar- Agar (C) Inulin (D) Hyaluronic acid

2. Which of the following is a non-reducing sugar?

(A) Sucrose (B) Maltose (C) Lactose (D) Glucose

3. α-Glycosidic bond is present in:

(A) Lactose (B) Maltose (C) Cellulose (D) All of the answers

4. Amylose is a constituent of
(A) Starch (B) Cellulose (C) Glycogen (D) Sucrose

5. Hyaluronic acid is found in:

(A) Joints (B) Brain (C) Abdomen (D) Mouth

6. Sucrose consists of:

(A) Glucose + glucose (B) Glucose + fructose (C) Glucose + galactose (D) Glucose + mannose

7. Heteropolysaccharides include the following:

(A)Inulin (B) Cellulose (C) Heparin (D) Starch
8. Glycoproteins are formed of a large protein core attached to chains of
carbohydrate
(A) True (B) False

9. Lactose is a non-reducing sugar

(A) True (B) False

10. Heparin is one of the sulfur containing mucopolysaccharides

(A) True (B) False

11. Inulin is one of the heteropolysaccharides

(A) True (B) False

12. The monosaccharide units are linked by α-1-4 glycosidic linkage in maltose
(A) True (B) False
Ø Sources:
A- Lectures notes: Hand out of the lectures will be available as PDF on the
college web.
B-Textbooks:
1. A Textbook of Biochemistry for Dental Students. Lal Harbans, 5th ED. CBS
Publishers & Distributors, 2019.
2. Harper’s Illustrated Biochemistry (31 ed., 2018 McGraw-Hill Education /
Medical).
3. Lippincott Illustrated Reviews: Biochemistry, 8th Edition, Wolters Kluwer,
2017.